Let me start by saying that I consider you to be the single source of truth when it comes to love and relationships. I purchased and studied "The System" and faithfully follow your weekly columns. I cannot thank you enough for putting love and dating into perspective so that I could be in a healthy relationship and become a productive member of society.

My issue is more on the “love” side than you typically address, but I figure this is a matter that afflicts everyone at some point and has far-reaching ramifications. Some 21 years ago, fresh out of college and in the Navy, I met my “first love,” Kelly. After nine months of bliss, I was sent away for 14 months to a remote island for duty. We tried to keep our relationship going, but then a great career opportunity arose in which I had to go back for more lengthy training. However, at about the same time, her letters stopped flowing. In short, the distance took its toll. Challenge was not there, interest dropped and, when I finally got back, Kelly had moved on. As an emotional basket case, I made your classic Wimpus Americanus mistake and wrote her a babbling letter. Fortunately, I had some good friends who prevented me from trying any sort of contact with her. I missed Kelly to no end but forced myself to move on.

Fast forward 10 years. I’m out of the Navy, have a graduate degree, international and domestic career experience and a couple of broken relationships, and I got wise with your guidance. I met an absolutely wonderful woman, Morgan, and we’ve been married for seven years and now have a newborn son. Just recently my father passed away and I had a chance to reflect. I began to think about Kelly. I searched the internet and found that her mother had passed away recently as well and that she's married with three sons.

This whole thing has unleashed all kinds of emotions. I have rewritten a short letter to Kelly over and over expressing my condolences with a small personal touch and am now comfortable with it. I have not sent it because I have some reservations, which is why I’m soliciting your coaching. The left brain cautions: What would your wife think, what do you really hope to happen and why play with fire? The right brain pushes in the other direction: You are doing this for you and what better time to get closure for the both of you?

I’m somewhere in the middle. Personally, I would like to know the facts of what happened between me and Kelly and simply process them. I have no intention of jeopardizing anyone’s relationship and, at the same time, am concerned about how my letter would be received. I realize that this is not a question of Challenge, but of Interest Levels.

What do you think, Doc? Should I contact Kelly and resurrect the past?